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Virginia Ann Isaac has had a long and varied career in the legal field. Virginia Ann began their career in 1995 as a Lawyer and Pupil at Toh Tan & Partners. In 1998, they moved to K. K. Yap & Partners, where they worked as a Lawyer. From 2000 to 2005, they worked at Baker McKenzie, where they held the roles of Junior Professional Support Lawyer and Paralegal. From 2005 to 2009, they were a Partner at Bale Living. In 2009, they joined Hip Product Factory Pte Ltd as a Director. From 2015 to 2019, they worked at The Law Society of Singapore, where they held the roles of Project Manager, Senior Executive Officer, and Executive Officer. In 2019, they began working at Next 10 Ventures as Manager, Business & Legal Affairs.

Virginia Ann Isaac attended St. Anthony's Convent Secondary School from 1984 to 1987. Virginia Ann then attended Raffles Junior College from 1988 to 1989. Finally, they completed a Bachelor of Laws - LLB at the National University of Singapore from 1990 to 1995.